Sodium Carbonate → (R)-N-(1-(4-formylphenyl)ethyl)methanesulfonamide

HRID 1483024

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-:16].[Na+].[Na+].C([SiH](CC)CC)C.[C]=O>CN(C=O)C>[CH:15]([C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1)=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

Combine N-[(1R)-1-(4-bromophenyl)ethyl]-methanesulfonamide (10 g, 35 mmol), (1,1′-bis(diphenylphosphino)-ferrocene)palladium(II)chloride (733 mg, 0.9 mmol), sodium carbonate (3.81 g, 35 mmol) and DMF (50 mL) in a 300 mL PARR reactor. Add triethylsilane (11.6 mL, 0.72 mmol) and purge the reactor with carbon monoxide three times. Charge the reactor with carbon monoxide (50 psi); seal; and stir the mixture at 90° C. for 15 hours. Cool the reactor to ambient temperature; filter the resulting mixture over Celite® pad; and wash the pad with DCM (150 mL). Collect the filtrate and sequentially wash the filtrate with water then brine (2×80 mL). Concentrate the organic filtrate under reduced pressure to obtain the residue as an orange oil. Purify by silica gel flash chromatography eluting with hexane/EtOAc (0 to 30% EtOAc) to provide the title compound (5.6 g, 70%, ee>98%). MS (m/z): 228 (M+1).

Aufarbeitung

customseal
temperatureCool the reactor to ambient temperature
filtrationfilter the resulting mixture over Celite® pad
washand wash the pad with DCM (150 mL)
customCollect the filtrate
washsequentially wash the filtrate with water
concentrationConcentrate the organic filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-77e918318dff4ba7a06fb4c1fea5dc27
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09416138B2

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